


when dean met castiel

by dannydevito420



Category: Supernatural
Genre: Alternate Universe, M/M, When Harry Met Sally AU, i wrote this for an audience of like three
Language: English
Status: In-Progress
Published: 2020-11-15
Updated: 2021-01-07
Packaged: 2021-03-10 04:15:56
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,479
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27577727
Author URL: https://archiveofourown.org/users/dannydevito420/pseuds/dannydevito420
Summary: "it only took three months... twelve years and three months."
Relationships: Castiel/Dean Winchester
Comments: 4
Kudos: 27





	1. ten years ago

**Author's Note:**

> the au no one asked for

**Summary for the Chapter:**

> _"I was sitting with my friend Arthur Cornrom in a restaurant. It was an cafeteria and this beautiful girl walked in and I turned to Arthur and I said, "Arthur, you see that girl? I'm going to marry her, and two weeks later we were married and it's over fifty years later and we are still married."_

It was a quarter past noon and his ride was officially late. Castiel Novak was about to leave college and embark on the journey that would begin the rest of his life, and his ride was late. Though that’s what he gets for trusting his friend Anna to connect him with her boyfriend. Anna’s taste in men was not what Castiel would call “acceptable” but sadly there were few people at the University of Chicago making the road trip to New York City. Before he really begins to regret his decision, an old Chevy Impala rumbles to a stop in front of Castiel. 

“I told you he was on his way!” Anna, who’d been waiting with Castiel, runs to the car as a young man wearing a beat up leather jacket and a red flannel steps out to embrace her.

They kiss, and then kiss again, and then they’re making out in the middle of the road, as if they’ve completely forgotten Castiel standing there with his luggage. 

He clears his throat in hopes they break apart but its barely heard between the sloppy exchange of wet kisses. Castiel rolls his eyes and coughs louder.

“Oh, I’m sorry! Castiel, this is Dean Winchester. Dean, this is Castiel Novak.”

Her boyfriend nods, “Nice to meet ya. The back’s open.” 

Castiel grabs his bags, really it’s his whole life stuffed in a few duffels, and places them in the trunk. As he does, he can hear Dean promising Anna to call her as soon as they arrive in New York. They start to kiss again, this time in between sappy “I love you”s and “I’ll miss you”s. Castiel slams the trunk with a loud “thunk”, startling the couple again. 

Castiel gives out a half-sincere “Sorry!” before making his way to the passenger side of the car. Dean slides behind the wheel, starting the engine, and Anna waves them off as they head east off campus.

* * *

They’ve not been driving long when Castiel lays out the plan for Dean.

“I’ve got it all figured out. It’s an eighteen hour trip, which breaks down into six shifts of three hours each, unless we want to go by mileage, I brought a map and I marked where we can switch.”

Dean swings an arm behind him, rummaging in the back for his cooler where he’s packed a large family size bag of potato chips. Eyes half on the road, half on the food, he replies to Castiel with a “sure thing” before offering the bag of chips to Castiel. 

“Oh no, thank you, I don’t eat between meals.”

Dean continues munching on his snack, and it’s silent in the car for a minute or two.

Dean breaks the quiet.

“So, Cas, why don’t you tell me the story of your life?” 

This man he has known for ten minutes calls him Cas and Castiel would correct him but he doesn't find it worth his trouble. But Dean asks him this question in a manner that is so nonchalant it throws Castiel off. Not many strangers in his life have asked him such a personal question, or bestowed a nickname, in such a short about of time of meeting him.

He tells the truth. “The story of my life hasn’t happened yet. Nothing’s happened to me. That’s why I’m going to New York.”

“To do what?”

“I’m going to journalism school to become a reporter.”

“So you can write about other people doing things.”

Castiel is thrown, again. This Dean Winchester is sharp, matter-of-fact, and just a bit rude but not so much that it bothers Castiel. 

Dean speaks, “Suppose nothing happens to you. Suppose you lived out your whole life and nothing happens, you never meet anybody, you never become anything, and finally you die in one of those New York deaths which nobody notices for two weeks until the smell drifts into the hallway.”

Castiel stares at Dean. Who was this man he was stuck with for the next eighteen hours?

“You sure have a dark side, Dean.”

“Of course I do. I bet you’re on of those perpetually happy people with stars in their eyes.”

“Well sure, I would say I’m a fairly happy person.”

“Do you ever think about death?”

“I guess.”

“You guess. Not me. Cas, I think about death all the time. When I buy a new book, I always read the last page in case I die before I finish it.” 

“That doesn’t make you deep. That makes you morbid.” Castiel retorts.

“I’ve seen shit and when it comes down to it, I’m gonna be ready and you’re not.”

“Meanwhile, you’re ruining your whole life waiting for ‘it’.”

Dean glances at Castiel, finally he’s the one thrown in this conversation. He looks at Castiel as if he’s never been challenged like that before and it makes Castiel secretly smug that he could stand his own in this conversation.

* * *

They make their way through Illinois, Indiana, and most of Ohio before stopping for dinner. They pass the time discussing everything from worst college experiences (Castiel’s is oversleeping a environmental science midterm, Dean’s is blacking out at a campus bar and throwing up on his Doc Martens), to favorite books (Castiel, _Walden_ , and Dean, _Catcher in the Rye_ ). They don’t have a ton in common but Castiel can sense a friendly repertoire building between the two of them. Dean is interesting, funny, and far smarter than he seems. Dean loves old cowboy movies, has parts of _The Iliad_ memorized, and can talk, in detail, about the '70s rock scene. Cas has even accepted Dean's silly nickname. 

They’re discussing _The Titanic_ when they pull up to a seedy diner off the interstate. 

“You’re absolutely insane.” Dean is arguing with Cas.

“I am not!”

“You would’ve stayed with freaking Billy Zane over young Leonardo DiCaprio?!”

“I would to save my family from financial ruin!”

“You’d rather be in a passionless marriage.”

“Than poor? Absolutely!”

Dean turns off the Impala’s ignition and steps out of the car. 

“Hm, I understand.” 

“What?” 

Dean starts walking away. 

“What, Dean?”

“Nothing, Cas, forget about it.” He waves Cas off. 

“No, seriously, tell me.”

They enter the diner.

Dean turns to Cas and stops. “You’ve obviously never had great sex.”

Cas is flabbergasted. “I have too! I’ve had plenty of great sex!” 

The patrons stare at him and Cas realizes just how loud his outburst was. He exasperatedly follows Dean to the booth he’s already sat at. He slides in on the other side of the plastic covered seat, flustered, and smoothes down the front of his shirt.

“With whom?”

“What?”

Dean looks up from his menu, “With whom have you had this great sex with?” 

Shocked, Cas stutters, “I’m not telling you!”

“Alright.” Dean shrugs, nonplussed, and looks back down at the menu. 

A beat.

“Ishim, if you must know.”

“Ishim?! Like Intro to PoliSci TA Ishim?! No.” 

“What, ‘no’?”

“You did not have great sex with your TA. Especially Ishim. Want to know how the electoral college works? Ask Ishim. The socio-economic politics of the Middle East? Ishim’s your guy. But slamming ass is not Ishim’s speciality.”

Cas scoffs as the waitress walks up to their table.

“What can I get y’all?”

“I’ll have the cheeseburger, please.” Dean orders.

“I'd like the chef salad please with the oil and vinegar on the side and the apple pie a la mode. I'd like the pie heated and I don't want the ice cream on top I want it on the side and I'd like strawberry instead of vanilla if you have it if not then no ice cream just whipped cream but only if it's real if it's out of a can then nothing but the pie.”

Both the waitress and Dean look at Cas like he’s from another planet. The waitress walks away to the kitchen as Dean shakes his head.

“What?” Cas innocently asks.

“Nothing, nothing.” Dean replies. “So why did you break up with Ishim?”

“How did you know we broke up?”

“Cuz you wouldn’t be here with me if you hadn’t, you’d be with Big Dick Ishim.”

“Dean! Not that it’s any of your business but I broke up with him because he was very jealous.” 

Dean hums in interest. 

Cas continues, “And just so you know, I am not “with” you.”

Dean raises an eyebrow.

* * *

Cas is calculating the tip for their meal when he catches Dean staring at him.

“What?” He touches his cheek. “Do I have something on my face?”

“You’re a very attractive person.”

Cas blushes, a deep red. “Thank you.”

They get up to leave the diner, walking towards the Impala.

“Anna never mentioned how attractive you are.”

“Well probably because I don’t play for her team.”

“Still, objectively, you’re attractive.”

“Excuse me, but you are dating Anna.”

“So?”

“So?! You’re hitting on me!”

Dean scoffs, “I am not.” He stops at the car door. “Ok, let’s say I was. What do you want me to say now? I take it back? Alright, I take it back.”

Cas stands on the opposite side, across the car. “You can’t! You already said it." He takes a deep breath. "Let’s just pretend it didn’t happen.”

They open their doors and get into the car.

“So what do you want to do for tonight? Go to a motel?” Dean winks. “See what I did is I didn’t pretend it never happened.”

“Dean.” 

“What?”

“We’re gonna be friends. Okay? That’s it.” 

“Great! Friends.” 

Dean starts the ignition and gets back on the interstate, climbing in speed.

Castiel props his arm on the window and leans his head on his hands, looking out at the fields zipping by and the dark night sky stretching on and on. On his face is a soft smile. The gentle sounds of Joni Mitchell’s _Blue_ play on the speakers when Dean suddenly speaks.

“You know, we could never really be friends.”

“Wh-Why not?”

“Seriously, and don’t take this as a come on, it’s strictly scientific, but you can’t be friends with someone you find attractive.”

“That’s not true at all, I have plenty of friends I would say are good-looking and sex is totally not involved.”

“No, you don’t.”

Cas looks at him quizzically, “Yes, I do.”

“You don’t.”

“Are you saying I don’t have friends?”

“No, I’m saying they all want to sleep with you. It’s human nature.”

“Is not. And no, they don’t!” 

“No person can be friends with someone they think is attractive, they’ll always want to have sex with them.”

“What if the person doesn’t want to have sex with them?”

“Doesn’t matter, one of you is already thinking about it and so the friendship is cursed.”

Cas pauses, thinks.

“Then I guess we can’t be friends.”

Dean looks at him from the corner of his eye. “Guess not.”

“Shame. You were the only person I knew in New York.”

They look at each other. There’s a twinkle of something in Dean’s eyes and Cas’ stomach does a little swoop.

* * *

Dean slows the Impala to a stop in front of the Union Square park entrance and pops the trunk. They both get out and walk to the back, Cas takes his bags and slings them over his shoulder.

“Thanks for the ride, Dean.”

“Yeah, no problem.”

Cas extends his hand. “It was nice knowing you.”

Dean smiles and shakes Cas’ hand. “Have a good life.”

Cas smiles back. “You too.”

Cas turns his back to Dean and the Impala and walks away. If he had turned around, he would've seen Dean leaning on the Impala, watching Cas disappear into the crowd.

**Notes for the Chapter:**

> i’m not much of a writer but this is just part 1, i hope to continue working on this and finishing it by the new year


	2. five years later

**Summary for the Chapter:**

> _"...Thirty four years later that I was walking down Broadway and I saw her come out of Toffenetti's."  
>  "And we both looked at each other, and it was just as though not a single day had gone by."  
> "She was just as beautiful as she was at sixteen."  
> "He was just the same. He looked exactly the same." _

**Notes for the Chapter:**

> remember when i said i'd finish this by the new year lol

“Delta Flight #727 to Los Angeles, now boarding.”

Dean shoulders his duffel bag with a huff, narrowly avoiding the bustling airport crowds. He hates airports. Really, he hates flying. He quickens his pace with purpose, when out of the corner of his eye he thinks he sees someone he recognizes. 

Dean approaches the man, who is currently in a lip lock with what looks to be his boyfriend.

“Balthazar?” 

Surprised, Balthazar unlatches himself from his partner to shake Dean’s hand.

“Dean Winchester! Jolly good to see you.” 

“Yeah, yeah, same here. How are you, you still at the mayor’s office?”

“Moved on up to the governor’s.”

“Wonderful!” Dean claps him on the arm.

Balthazar puts his arm around the shorter man next to him, “Dean, let me introduce you to Castiel Novak.”

Dean makes eye contact with Balthazar’s boyfriend and for one second, he feels a jolt run through his body. Then just as fast as it came, it disappears. 

Dean grins, “Nice to meet you.”

This Castiel gives Dean a tight-lipped smile in return. 

When Dean walks away, Castiel lets out a breath of relief. 

“Thank God he didn’t recognize me. Five years ago, after graduation, I drove him from Chicago to New York and it was the longest night of my life.”

“How so?” Balthazar asks.

“He hit on me and he was dating my friend at the time! Oh shoot- what was her name? April? No, Anael? Damn, I’m only 26 and my memory is completely shot.”

“What happened?”

Castiel, lost trying to remember the name, is confused. “Huh?”

“When Dean made a pass at you.”

“Oh, I rejected him and he said we could never be friends if we were attracted to each other- Anna! That was her name, Anna!” 

Balthazar looks at him, amused.

“I’ll miss you. I love you.”

Castiel is thrown off, he wasn’t expecting this for at least a few more weeks. 

Automatically, he returns the sentiment, “I love you too.”

He throws his arms around his boyfriend, squeezing tight.

Balthazar gives him one last kiss before letting Castiel leave for his flight.

* * *

Twenty minutes into the flight, as Castiel is ordering a drink from the stewardess, he hears a voice from five years ago.

“University of Chicago!”

Castiel looks behind his shoulder and sees Dean Winchester leaning in his seat. He never thought he’d see those green eyes again. They still have just the slightest devilish twinkle to them. Dean’s hair has grown out, it now swoops in long locks and falls above his eyes. Where he was babyfaced before, he now sports long brown stubble. To Castiel’s not-so disappointment, time has been Dean’s friend, he looks fantastic, whereas Castiel believes he himself has only aged in a decline.

He replies in the affirmative, sipping his ginger ale.

Dean looks him up and down, obviously checking him out. Cas cannot lie to himself, it secretly thrills him.

“Did you look this good in college?”

Castiel blushes. “I-“

Despite the staring, he knows Dean still cannot place him. 

“Did we ever.. ya know?” Dean waggles his eyebrows suggestively. 

Castiel blushes an even darker shade of pink, “No! We drove together from Chicago to New York after graduation.”

Dean snaps his fingers, “that’s right!” 

Mistaking their interaction for a happy reunion, the nice and quiet man sitting next to Castiel offers Dean to switch seats so they could catch up, which Cas definitely did not want to do. It took Castiel a better part of a month to forget about the freckles across Dean’s cheeks and the pink bow of his lips. He did not need any old feelings cropping up right now, he likes Balthazar very much, thank you. No, sorry, he _loves_ Balthazar. 

“So you’re with ol’ Balthazar, huh Cas?” 

Just like that, he’s back in the front seat of some black sports car with a stranger who acts like they’ve known each other their entire lives. It was jarring then, and it’s jarring now. No one has called him Cas since Dean.

Cas tries to be annoyed, really he does, but there’s something about Dean he finds compelling.

“Yes.”

“Nice guy. You’ve been together, what, a month?”

“How did you know?”

Cas almost forgot how candid and astute Dean was.

“He dropped you off at the airport, only new relationships do that. That’s why I never take someone to the airport, that way they don’t expect it every time they go out of town.”

“You haven’t changed a bit, Dean Winchester.”

Dean clutches his chest, pretends to be insulted.

“Au contraire! I am a new man.” 

He lifts his left hand and reveals a wedding ring.

Castiel laughs, despite himself. “You’re married?!” 

Dean looks at the ring, then at Castiel. “Engaged.”

“I find it hard to believe you’d ever settle down.” 

“You’d like her.”

Cas raises an eyebrow, he doubts that.

“Her name’s Lisa, she’s a yoga instructor. Very bendy.” Dean winks. 

“I cant believe _you’re_ getting married. It’s so… idealistic of you!” 

“Hey, that’s what falling madly in love will do. And, well, you get to a certain point where you’re tired of the whole bachelor lifestyle.” 

Cas notices a solemn look falling across Dean’s face, a slip of the charismatic mask, a chink in the resolute armor. 

“Dating in the city is a nightmare, how many first dates can one go on. I mean, you go to dinner, maybe a movie, then it’s back to their place and sure the sex is good, sometimes great. Sometimes it’s bad. Then it’s over and you’re in the dark wondering how long you gotta lay there, holding them.” 

He glances at Castiel, whose face is so open and earnest it shakes Dean out of his diatribe. 

“See, most guys don’t want to be held at all, where women need to be held all damn night.”

“I like to be held.” Cas confesses. 

“Of course you do.”

Cas gives him an offended look.

Dean backpedals, “No, no, I’m not saying that’s a bad thing. I just know you’re romantic like that. But see that’s another part of the problem, if you think women are hard to understand, gay guys are even worse. You gotta figure out if the guy you just plowed now wants you to cuddle, it’s exhausting. Try navigating both the male and female dating scenes, it’s enough to make anyone marry the first person they see.”

Cas ignores the underlying cry for help, he’s sure Dean wouldn’t want to talk about it anyway.

“Is that really what they think about? How long to hold someone for?” 

“Guarantee it.”

Cas knits his brows, looks down at his soda in contemplation.

* * *

Cas loses Dean once they land in Los Angeles and grabs his luggage off the trolley. He starts walking towards the exit when a figure appears on his left.

“So did you ever become a journalist?” Dean picks up where they left off at the gate. 

Castiel thought he had managed to shake him but it seems with Dean that is an impossibility. 

“I did. I work at _The News_.”

“Good for you!”

“Thank you. What about you, Dean? Did you ever figure yourself out?”

Dean shrugs, a little embarrassed. “I’m a lawyer. It pays the bills.”

Cas looks in his eyes and sees a glint of sadness but then Dean blinks and it’s gone. It’s the same look he saw when Dean talked about his fiancé.

Dean makes haste to change the topic, “Would you like to get dinner?”

It’s not a good idea, Cas tells himself. He thinks of Balthazar. He thinks what Dean would look like naked. He thinks of Balthazar.

“C’mon, just a friendly dinner.” Dean prods.

“I thought we couldn’t be friends.” 

Dean looks at him confused, “What?”

“Five years ago, you said people who are attracted to each other cannot be friends.”

“I said that? Really?” He pauses. “Oh yeah, no, I definitely said that. It’s true.”

Castiel continues walking down the airport hallway, quickening his pace just a bit. Dean Winchester just manages to get underneath his skin without trying. 

Dean jogs to catch up, “See there’s an amendment to said rule. If both parties are involved with other people,” He gestures between him and Castiel. “Then the question of sex is off the table. Totally platonic.” 

“Uh-huh.” Cas adjusts the tie hanging from his neck.

Dean continues his soliloquy, “Well actually, that doesn't work either because then your partner can't understand why you need to be friends with the person you're just friends with. Something must be missing from the relationship so you’re going outside to get it. Then you deny everything, you say “we’re just friends” but they accuse you of being secretly attracted to your friend, which I mean, come on, who the hell are we kidding, of course we are. Which brings us back to the original rule, so where does that leave us?”

Castiel stops in front of the exit doors and faces the jabbering man head on.

“Dean.”

“Hmm?”

“Goodbye.” Cas says, with a resolute finality.

Dean looks disappointed, then acquiesces. “Oh, okay. Bye, Cas.”

Castiel tilts his head and then walks out the door and into the taxi line, once more leaving Dean behind him.

**Notes for the Chapter:**

> please forgive the angel incest, i hate having to use other angels as cas' significant others but he's literally never interacted with anyone else. also for what dean looks like in this chapter, imagine quarantine jensen. who knows when i'll write chapter 3


End file.
